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Find 5 Star Hotels in Olowalu, HI from $566

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Compare Olowalu 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Club Suite, 1 Bedroom | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Four Seasons Resort Maui at Wailea
5.0 star property
9.6 out of 10, Exceptional, (1001)
"We had a great stay for my wife’s birthday. The atmosphere and service was great and it was busy but we did not feel crowded. We did have a small issue with council works outside our room and after explaining things to management they kindly moved us to another room away from the works. Looking forward to staying here again"
The price is $995
$1,174 total
includes taxes & fees
May 18 - May 19
Four Seasons Resort Maui at Wailea
2 bars/lounges, 2 poolside bars, swim-up bar
Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
9.0 out of 10, Wonderful, (1000)
"Potentially the most beautiful (semi all inclusive) resort in Maui. It was a treat and a delight to stay here. M"
The price is $756
$950 total
includes taxes & fees
May 9 - May 10
Grand Wailea Maui, A Waldorf Astoria Resort
7 restaurants, breakfast served
Four Seasons Resort Lanai
5.0 star property
9.8 out of 10, Exceptional, (198)
"You haven’t been anywhere until you’ve experience pure luxury of the four seasons hotel in Lanai. Service at its best. Class and attention to every detail. The most beautiful hotel on the planet "
The price is $1,345
$1,587 total
includes taxes & fees
May 27 - May 28
Four Seasons Resort Lanai
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Outdoor spa tub
Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
9.2 out of 10, Wonderful, (944)
"This hotel is a total gem. It's a rare adults-only property in Hawaii, and the amenities are everything you need, nothing you don't. The bar is perfect, the restaurant is great (especially for breakfast or a celebratory dinner), and the pool bar is first rate. Best Mai Tai we had in Maui! If you prefer boutique hotels and want a quiet experience with a lovely suite, look no further!"
The price is $899
$1,108 total
includes taxes & fees
May 4 - May 5
Hotel Wailea, Relais & Chateaux - Adults Only
3 outdoor pools, cabanas (surcharge), sun loungers
The Ritz-Carlton Maui, Kapalua
5.0 star property
9.2 out of 10, Wonderful, (1003)
"Amazing facility, great staff, always attentive and great for families!"
The price is $949
$1,159 total
includes taxes & fees
May 5 - May 6
The Ritz-Carlton Maui, Kapalua
Breakfast, lunch, dinner served; alfresco dining
Sensei Lanai, A Four Seasons Resort
5.0 star property
9.6 out of 10, Exceptional, (115)
"This property was absolutely breathtaking. Outstanding service and beautiful rooms Highly recommend "
Sensei Lanai, A Four Seasons Resort
Outdoor pool, sun loungers
Ho‘olei Villas at Grand Wailea
5.0 star property
9.6 out of 10, Exceptional, (36)
"This is an amazing place to stay with a family. Views. Facilities. Local entertainment, dining, shopping, and activities."
The price is $1,902
$2,302 total
includes taxes & fees
May 8 - May 9
Ho‘olei Villas at Grand Wailea
On the beach, beach towels, snorkeling, surfing
Montage Kapalua Bay
5.0 star property
9.8 out of 10, Exceptional, (190)
"Beautiful resort!"
The price is $1,199
$1,484 total
includes taxes & fees
May 24 - May 25
Montage Kapalua Bay
View from property
Fairmont Kea Lani Maui Villa Experience
5.0 star property
10.0 out of 10, Exceptional, (3)
"Good property "
The price is $3,029
$3,632 total
includes taxes & fees
May 22 - May 23
Fairmont Kea Lani Maui Villa Experience
Outdoor pool
Hale Kai at Maui Kamaole
5.0 star property
Hale Kai at Maui Kamaole
Property grounds
Kalea at Kuleana
5.0 star property
Kalea at Kuleana
Condo, Multiple Beds, Balcony, Pool View (F-203) | Living area | TV
Kihei Garden Estates F-203
5.0 star property
Kihei Garden Estates F-203
Outdoor pool
Hale Hau'oli
5.0 star property
Hale Hau'oli
Luxury Apartment | Private kitchen | Full-size fridge, microwave, oven, stovetop
Wailea Luxury Hilltop Resort Vista
5.0 star property
Wailea Luxury Hilltop Resort Vista
Outdoor pool
Kaia at Ekahi
5.0 star property
Kaia at Ekahi

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Olowalu.
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr, Lahaina, HI
The price is $566 per night from May 16 to May 17
$566
$721 total
includes taxes & fees
May 16 - May 17
9/10 Wonderful! (1,002 reviews)
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Ready to experience the next standard in luxury? We know you're thinking about it. Add even more pleasure on your next trip to Olowalu by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Olowalu any longer. You'll join the multitudes of vacationers who have made Olowalu so fashionable in the last few seasons. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. You deserve an outstanding getaway. Our 5-star hotels in Olowalu are the perfect places to relax in during your next escape.

Book the Best Olowalu 5-Star Hotels

You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and one-on-one attention are all at your fingertips. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A body scrub that will leave you feeling refreshed and alive? 24-hour room service, so you can order that Turkish coffee in the wee hours of the morning? A Swedish massage to help your cares fall away? Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

Can't wait to get outside? We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Olowalu are the perfect place to relax after a busy day.

Your Getaway Starts Today

The results are in, and Olowalu 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Your great getaway is just a mouse-click away -- Expedia can help you land a great deal on accommodation. Opt for one of Expedia's Olowalu 5-star hotels today and relax in total tranquility at your convenience.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Olowalu?
How much you pay for a 5-star hotel in Olowalu depends on factors like when you plan to travel and the length of your vacation. Our top tip for landing the best deal? Use our pricing filters to compare the available accommodations for your preferred dates.

  • Search for the lowest price per night from $566

What makes a hotel 5 stars in Olowalu?
From gourmet dining venues and fitness centers to pools and superior bedding, the 5-star experience in Olowalu is all about luxury and relaxation. But it calls for more than just top-notch amenities to get a 5-star rating. Hotels must also provide exceptional guest-centric services like in-room massages, dry cleaning and laundry and concierge services.
Are there any 5-star all-inclusive resorts in Olowalu?
Use our filter tool to find a high-end retreat in Olowalu where most of what you need is included in the price. After your initial search, refine your results for hotels that have a rating of 5 stars and are listed as “All inclusive.” The most important thing on the agenda at these stays? Pure enjoyment and indulgence.
Are there any 5-star vacation rentals in Olowalu?
You won’t find any 5-star vacation rentals in Olowalu on our site, but there are a few other top-rated options worth looking into. Browse our vacation rentals in Olowalu to book the perfect place for your getaway.

Recent reviews of Olowalu hotels
Expedia verified reviews

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5/5 Excellent
"Amazing facility, great staff, always attentive and great for families!"
A verified traveler stayed at The Ritz-Carlton Maui, Kapalua
Posted 8 days ago
The Ritz-Carlton Maui, Kapalua